Tetrahedron p. 3715 - 3722 (1986)
Update date:2022-07-31
Topics:
Farina, Francisco
Maestro, M. Carmen
Martin, M. Rosario
Martin, M. Victoria
Sanchez, Felix
Soria, M. Luisa
The reactions of 3-bromo-5-methoxyfuran-2(5H)-one (1) with nucleophiles in acetonitrile, in the presence of potassium carbonate and tetrabutylammonium bromide as a catalyst, are reported.The bromofuranone 1 reacts with several carbon and oxygen nucleophiles to give the cyclopropane bis-lactones 7, 8, 11 or 12.When 1 is reacted with diethylamine or propane-2-thiol in a 2:1 ratio, similar cyclopropane bis-lactones 16 or 21, respectively, are formed.This behaviour is explained on the basis of a mechanism involving a double Michael addition, followed by ring closure via internal nucleophilic substitution of the halogen.
View MoreAntaeus Bio-technology Co., LTD(expird)
Contact:021-31252569
Address:shanghai pudong
Contact:86-21 60347964
Address:No.1304, West Meilong Road, Minhang District, Shanghai, China
SuZhou Bichal Biological Technology CO.,LTD
Contact:+86-512-68051130
Address:NO.32 huoju road HI-TECH Industrial development zone SuZhou China
Contact:+86-0512-69209969
Address:Room 317,Lushan Road,Suzhou New District,Jiangsu Province,China.
Jiaxing Carry Bio-Chem Technology Co.,Ltd
website:http://www.carrybiotech.com
Contact:0573-82788958
Address:Add.Fl 3th, Pharm Vally,Kaichuang Rd, Xiuzhou District, Jiaxing, Zhejiang,314031,China
Doi:10.1039/c6cc09493g
(2017)Doi:10.1002/anie.201806157
(2018)Doi:10.1021/jo9722360
(1998)Doi:10.1039/c1gc15191f
(2011)Doi:10.1248/cpb.46.255
(1998)Doi:10.1016/S0040-4020(01)96647-5
(1985)